Item delivery optimization provides for dynamic delivery route optimization when a destination may be mobile. In some situations, recipients for ordered items may be mobile and/or ray be situated at a non-fixed location. For example, restaurant food ordered via counter service may need to be provided to patrons who are free to select their own table, or medications may need to be delivered to patients in a hospital who may move from room to room for exams, tests, procedures, etc. Similarly, mail packages may need to be delivered to office workers whose work locations may change due to reorganizations, remodeling, travel between office locations, meetings in conference rooms, etc. Conventional approaches address this problem by delivering the items to a location specified at the time the order is placed, or by forcing the delivery courier to locate the recipient manually. These approaches often result in delays in the delivery.